How Hopin’s CCO Knew a Startup Environment Was Right For Her—and Two Questions to See If It’s Right for You

If there's a thread that connects all the different facets of Rosie Roca's life, it's the power of bringing people together.

From how she was raised, to how she got her first job, to the decision to leave enterprise software to take on her current role as the Chief Customer Officer at fast-growing events technology platform Hopin, a focus on community has helped to guide Rosie's decisions.

We sat down with Rosie to talk about her career, her new role at Hopin, and what advice she has for people who think that their ideal community might be at a startup.

Drawing from experience

Growing up in Havana, Cuba and moving to the United States when she was 12, Rosie's first values were drawn from the community she was raised by. "I was surrounded by really hard-working folks that just forged paths ahead of them no matter what obstacles were in the way," she says. "It's really transformed how I think about challenges and it gave me a framework, from a grit and perseverance perspective, that I carry with me."

Her interest in how other communities worked and were run led her to study government at Harvard. "Growing up in a country like Cuba, you come away with a different understanding or appreciation for government structures and political systems," she says. "I was fascinated by the differences between my native country and the U.S., and what you see around the world."

As an undergraduate, she traveled to the United Kingdom and Spain, and studied abroad in France, working toward an international law degree. "I tested that notion, which I encourage everyone [to do]," she says. "I took a law school class my senior year of college. I absolutely loved the discussion and didn't enjoy everything else about it!"

It was at a conference about sports that Rosie found her first job. (The irony of the importance that well-run events have had on her career is not lost on the Hopin leader!) Rosie listened to the keynote speaker talk about how passionate she was about her work and happened to sit next to her at lunch after her talk.

"We hit it off," explains Rosie. The keynote speaker also happened to be looking for someone to help her with a marketing-research role, including interviewing customers about their experience. Rosie was the perfect fit.

Her role drew on the research skills she'd honed as an undergrad, and Rosie loved the community she found at work. The company, Kraft Sports Group, ran the New England Patriots and Gillette Stadium, and Rosie spent her days interviewing fans and customers of major events. "We were helping the business better understand the voice of the customer," she says.

Finding success in customer success

Rosie found herself interested in how technology could drive the future of the fan experience and community, and how marketing would be transformed around that technology. She went to Stanford for her MBA to learn more about those areas.

One professor stuck with her. His point? "'At the end of the day, no matter what role you go into, you're going to have to learn how to sell. How to sell your ideas, how to bring along hearts and minds, how to think about selling a product or a service,'" says Rosie. She liked the idea of selling, but didn't have much experience in it, so she took on a role at an early stage startup RelateIQ, which later became part of Salesforce, on their customer success team.

"It was early days in customer success," she says. "The strength I had, coming from my background, was that I had no fear in picking up the phone, understanding insights, and helping the business to react from an operational perspective."

Once again, Rosie found herself in a position where she worked closely with a community, this time one made up of Salesforce customers. She worked to understand their goals and frustrations, to support them, and help create better products for them.

"The foundational aspiration [of customer success] is to really understand how a business connects to its customers to support them in achieving their goals," she says. "What made me successful in that opportunity and every one after that was to stay focused on the user."

Rosie rose through the ranks, from manager to director to SVP, and was enjoying the challenge of setting a vision and getting a team aligned behind it. But she wanted to try doing that from scratch somewhere new. Somewhere like a startup.

Why Hopin

When Rosie first heard about Hopin, it seemed like a "once-in-a-lifetime opportunity."

"It is a totally new and exciting space to build a company, build a team, and build partnerships with customers in a whole new way, at a time when this type of technology is so needed," she says. "Ultimately, what drove my decision to join Hopin was the team of really talented folks, all passionate about the customer experience and the events industry,working together to create an iconic company."

What's most impressive to Rosie now, six months into her role, is the speed at which the business is growing and evolving. "It's unlike anything I've ever seen from an execution perspective," she says. "A week in prior roles is maybe a day at Hopin, which is a testament to our stage and to the type of culture that we have."

How can you know if Hopin—or another fast-growing startup—is the right next place for your career? Rosie has two key pieces of advice:

1. Make sure you're excited about the problem they're solving, and all the challenges that will come after it.

"Be super clear around your purpose and the challenges that motivate you and will push you into that uncomfortable zone, which is where we do a lot of our learning," she says. For her, at Hopin, that means not just building new event experiences for our customers, but also helping to redefine what overall customer success looks like.

2. Know who you'd be working with and learning from, and be comfortable with that.

Rosie comes at this part from two angles: First, who are you working for? Is your manager someone who can motivate people? "At Hopin, our CEO Johnny has the capability to drive execution and build team culture so quickly," she says. "He's been able to motivate hundreds of people in a year to do something that no one else has ever done before. I'm really learning from him and am thrilled to continue."

The second part? "Who are you going into the trenches with?" asks Rosie. Is it a team of people that you feel like you can trust and enjoy spending time with? That's been the case at Hopin, she adds: "They're so positive and optimistic and ambitious, with an incredibly impressive level of talent and execution."

Staying connected with her community

As busy as she gets, Rosie always makes time for one weekly (if not daily) ritual: reviewing the Slack channel dedicated to shouting out Hopin employees who are going above and beyond. "I go to that channel and just scroll and read about the camaraderie and the support that we have across the entire organization," she says. "You can't help but feel like, 'Holy cow, this is an incredible team, and everyone is really supporting each other in every way that they can.'"